The town was established in 1739 after the signing of a Peace Treaty with the English Occupation Army ending nearly five decades of a guerilla war. A few hundred poorly armed resistance fighters held off several thousand of King George III's finest soldiers forcing them to grant the Maroons freedom and 1500 acres of land.

Cudjoe (Kojo) was leader of all the Maroons in Jamaica and was headquartered in Trelawney Town. Accompong, Cudjoe's brother, was sent to Old Town to establish a village later to bear his name. This village was strategically located to protect Cudjoe's southern flank.

Following the terms of the Treaty, a Colonel is elected (in the old days for life but now 5 years) to lead the Leeward Maroons. The Maroon government is responsible for judicial matter within their territory except for cases of Capital Crime. There are no police stationed in the town and for 275 years this peaceful village has only had one case of Capital Crime.